Boatright, an Aurora, Illinois native, averaged 31.2 points per game as a senior at East Aurora High School and was named Illinois Co-Mr. Basketball with Chasson Randle. As a Senior, he once scored 63 points in a game against Proviso West, and another outing scoring 55 against St. Charles North. Boatright also led the charge in defeating and upsetting the undefeated Benet Academy Redwings in the Sectional Semifinals 60-52. Benet was ranked #1 in the State of Illinois, 7th in the Nation with a team that featured Wisconsin bound Frank Kaminsky. Boatright finished with 29 points and 6 assists. He had originally committed to West Virginia, but changed his mind when the Mountaineers signed another point guard just a day later.. He then went on and decided to commit to the University of Connecticut. Boatright was ranked 74th in the ESPN 100 list ofhigh school basketball players, and also was listed as 7th in the state of Illinois and 14th in the point guard position.
College career
Freshman year
Upon arriving at Connecticut, his eligibility was challenged. After missing the first three games, the National Collegiate Athletic Association ruled that he would have to serve an additional three-game suspension to bring his total to six games served due to "receiving improper benefits". Upon further review, Boatright endured a total of nine games under suspension. Nonetheless, he became a key player for the Huskies as a freshman, averaging 10.4 points, 4.0 assists and 3.3 rebounds in 30.1 minutes per game.
Sophomore year
Following his return, Boatright along with backcourt teammate Shabazz Napier both rose to the national spotlight as they were highlighted as one of the nation's best backcourts, as they both averaged a combined 33 points and 9 assists per game, outplaying nearly every opponents' backcourt they've played. He kept the momentum up in his sophomore season of 2012–13, raising his scoring average to 15.4. He was named to the USBWA All-District first-team at the conclusion of the season.
Junior year
On April 26, 2013, Boatright opted to return to the team for his junior year along with teammates Shabazz Napier and DeAndre Daniels. Boatright played 39 of UConn's 40 games, starting 38 of them, averaging 12.1 points, 3.4 assists, 1.6 steals and a career-best 3.5 rebounds. He averaged 13.5 points and 5.0 rebounds in the Final Four and was named to the All-Final Four team. He was one of four Huskies to average double-digit point totals in the inaugural American Athletic Conference Tournament. Boatright scored in double-figures in 27 of 39 games and in all six of UConn's NCAA Tournament games. He was second on the team this year with 61 steals, which were the most ever for him in a season. Boatright's defense was a key factor in the Huskies' drive to the 2014 Final Four. He was named to the 2014 All-Final Four team and UConn won the national championship.
Senior year
Upon the preseason of the 2014–15 season, Boatright was named the preseason All-American Athletic Conference player of the year and was selected to the preseason first team. He was then added to the 2015 Bob Cousy Award watch list. Boatright was a unanimous first-team All-American Athletic Conference team selection in 2015. He hit a game winning three off a crossover against Cincinnati in the AAC Tournament quarter-finals as time expired to win the game 57-54, which many considered was a mimic of Kemba Walker's game winning shot against Pittsburgh in the 2011 Big East Tournament.
After going undrafted in the 2015 NBA draft, Boatright signed with the Brooklyn Nets on July 2 and joined the team for the 2015 NBA Summer League. In nine Summer League games for the Nets, Boatright averaged 14.1 points, 2.3 rebounds and 2.2 assists per game. On October 20, 2015, he was waived by the Nets after appearing in four preseason games. On October 23, he signed with the Detroit Pistons, but was waived two days later. On October 31, he was acquired by the Grand Rapids Drive of the NBA Development League as an affiliate player of the Pistons. On January 21, 2016, he was waived by the Drive.
For the 2018–19 season, Boatwright signed with the Agua Caliente Clippers of the NBA G League. On December 16, 2018, Texas Legends announced that they had acquired Boatright from the Agua Caliente Clippers.
Europe
On January 8, 2019, Unicaja announced that they had acquired Boatright. On July 30, he signed for Cedevita Olimpija of the ABA League. On January 29, 2020, he has signed with BC Avtodor of the VTB United League.
Personal
Boatright is the son of Mike McAllister and Tanesha Boatright. He has one brother Michael and two younger sisters Dasia and Deahjay.